Hydroxymethylation of nitroalkylbenzenes with paraformaldehyde was accomplished by electrolysis in a (CH2O)n–DMF–Et4NOTs–(Pt electrode) system. The reaction was found to be catalytic (0.25 faraday/mol) and dependent on the electroreduction of formaldehyde and/or nitroalkylbenzene. A variety of nitroalkylbenzenes were transformed to their corresponding mono- and/or bishydroxymethylated derivatives in good yield. The product yield and selectivity were shown to depend on the order of reagent addition, solvent, supporting electrolyte, and structure of the starting nitroalkylbenzenes. A plausible mechanism of the generation of base catalysts (EG base) in electroreductive media is discussed.
ASJC Scopus subject areas
- Organic Chemistry